2-Methyl-3-hydroxypentanoic acid threo-3-pentyl ester | 114715-56-9

• 物质功能分类: 分析化学 - 标准品 - 药典标准品和杂质标准品
• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: 2-Methyl-3-hydroxypentanoic acid threo-3-pentyl ester
• 英文别名: 3-pentyl (2RS,3RS)-3-hydroxy-2-methylpentanoate；1-ethylpropyl 3-hydroxy-2-methylpentanoate；Pentanoic acid, 3-hydroxy-2-methyl-, 1-ethylpropyl ester, (R*,R*)-；pentan-3-yl (2R,3R)-3-hydroxy-2-methylpentanoate
• CAS: 114715-56-9
• 化学式: C₁₁H₂₂O₃
• 分子量: 202.294
• InChiKey: JZOCRUBSQNZLIW-PSASIEDQSA-N

物化性质

• 沸点：
  283.4±13.0 °C(Predicted)
• 密度：
  0.953±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Methyl-3-hydroxypentanoic acid threo-3-pentyl ester 在 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 121.0h， 生成 1-ethylpropyl (2SR,3RS)-3-hydroxy-2-methylpentanoate
  参考文献：
  名称：

  Mori, Kenji; Ishikura, Masaharu, Liebigs Annalen der Chemie, 1989, p. 1263 - 1266

  摘要：

  DOI：
• 作为产物：
  描述：

  3-戊醇 在 锌 作用下， 以 甲苯 为溶剂， 生成 2-Methyl-3-hydroxypentanoic acid threo-3-pentyl ester
  参考文献：
  名称：

  粮象鼻虫聚集信息素的化学鉴定

  摘要：

  （R *，S *）-2-甲基-3-羟基戊酸酯的乙基丙基被确定为（L。）（谷类象鼻虫）聚集信息素的主要成分。

  DOI：

  10.1016/s0040-4039(00)61831-2

文献信息

• New Synthesis of (<i>±</i>)-Sitophilate Using Carboxylic Acid Dianion Methodology - A Stereoselectivity Study
  作者：Margarita Parra、Salvador Gil、Pablo Rodriguez、Enrique Sotoca

  DOI：10.1055/s-2005-918466

  日期：——

  A simple two-step synthesis of (′)-sitophilate in has been developed by addition of propanal to the lithium enediolate of propanoic acid and subsequent esterification with 3-pentanol under standard Fischer conditions. Efforts to control the diastereoselectivity to generate the syn isomer are described. A modest degree of asymmetric induction is found using chiral amides as base.

  通过将丙醛添加到丙酸的烯二醇锂中并随后在标准 Fischer 条件下与 3-戊醇酯化，开发了一种简单的 (')-sitophilate 的两步合成。描述了控制非对映选择性以产生顺式异构体的努力。使用手性酰胺作为碱发现了适度程度的不对称诱导。
• Stereoselective chemoenzymatic synthesis of sitophilate: a natural pheromone
  作者：Dimitris Kalaitzakis、Spiros Kambourakis、David J. Rozzell、Ioulia Smonou

  DOI：10.1016/j.tetasy.2007.10.008

  日期：2007.10

  The aggregation pheromone of the granary weevil Sitophilus granarius, (2S,3R)-1-ethylpropyl 3-hydroxy-2-methylpentanoate, has been synthesized in 63% total isolated yield and high chemical and enantiomeric purity (98% de, > 99% ee) from readily available methyl 3-oxopentanoate. A stereoselective ketone reduction followed by an ester hydrolysis, were the two key steps of the synthesis and were both performed by commercially available enzymes. (c) 2007 Elsevier Ltd. All rights reserved.
• Stereochemically controlled synthesis of racemic sitophilate, the aggregational pheromone of the grain weevil
  作者：B. A. Cheskis、A. M. Moiseenkov、N. A. Shpiro、G. A. Stashina、V. M. Zhulin

  DOI：10.1007/bf00960333

  日期：1990.4
• Diastereoselectivity in heterogeneous catalytic hydrogenation of Baylis–Hillman adducts. Total synthesis of (±)-sitophilate
  作者：Cristiano R Mateus、Melissa P Feltrin、Ana M Costa、Fernando Coelho、Wanda P Almeida

  DOI：10.1016/s0040-4020(01)00647-0

  日期：2001.8

  We describe herein a highly diastereoselective total synthesis of racemic sitophilate, based on the results obtained in a diastereoselective heterogeneous catalytic hydrogenation reaction of a set of Baylis-Hillman adducts originating from aliphatic aldehydes. (C) 2001 Published by Elsevier Science Ltd.
• Synthesis of all four possible enantiomers of sitophilate, aggregation pheromone of the granary weevil
  作者：B. A. Cheskis、N. A. Shpiro、A. M. Moiseenkov

  DOI：10.1007/bf00961038

  日期：1991.11

  An efficient synthesis of the 3-pentyl ester of 2S-methyl-3R-hydroxypentanoic acid (sitophilate) and its 2S,3S-, 2R,3R-, and 2R,3S-isomers has been carried out starting from the available 2R-methyl-3-butenyl acetate as sole monochiral precursor.